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Séminaire Chimie ED459

Cycloisomérisation d’énynes et d’alcynes fonctionnalisés en présence de complexes d’iridium, de platine et d’or

Dr. Véronique Michelet, D.R. CNRS (Laboratoire Charles Friedel, UMR 7223 CNRS ENSCP Chimie ParisTech)

published on

Le Jeudi 24 Mars 2011 à 13h45
UM2, salle de cours SC-16.01

Over the past few years, significant research has been directed toward the development of new methodologies for synthetic efficiency and atom economy processes.[1] Among them, the potential of transition-metal-catalyzed reactions have been steadily demonstrated, as they give a direct and selective way toward the synthesis of highly valuable products. Several transition metals (Pd, Ru, Rh, Ir) and more recently gold and platinum have been used to perform C-C and C-heteroatom bond formation reactions.[2] We have been engaged in a wide project dedicated to the development of catalytic methodologies for the synthesis of original carbo-and heterocycles. Our interest has been focused on the cyclization of functionalized alkynes. An unprecedented selectivity was observed for homopropargylic alcohols and diols.[3] Simple and commercially available gold catalysts might also function as promoters for the reaction of other functionalized alkynes such as carboxylic acids, which gave rise to en efficient entry to functionalized lactones.[4,5] In the case of functionalized enynes,the use of platinum and gold catalysts promoted novel rearrangements, based on the addition of nucleophile to alkenes followed by the cyclization of the enyne.[6] Some novel systems (based on chiral platinum and gold complexes) have been developed for the asymmetric cycloisomerization of enynes, leading to good and excellent enantiomeric excesses.[7] This presentation will show an overview of the latest results.

Figure 1 (cliquer pour l’agrandir)

References

1. P.N. Anastas, M. M. Kirchhoff, Acc. Chem. Res. 2002, 35, 686.
2. D. J.Gorin, F. D. Toste, Nature 2007, 446, 395. A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208. A. Fürstner, P. W. Davies, Angew. Chem. Int. Ed. 2007, 46, 3410. A. R. Chianese, S. J. Lee, M. R. Gagné, Angew. Chem. Int. Ed. 2007, 46, 4042.
3. E. Genin, S. Antoniotti, V. Michelet, J.-P. Genê,t Angew. Chem. Int. Ed. 2005, 44, 4949. S. Antoniotti, E. Genin, V. Michelet, J.-P. Genêt, J. Am. Chem. Soc. 2005, 127, 9976.
4. E. Genin, P.Y. Toullec, S. Antoniotti, C. Brancour, J.-P. Genêt, V. Michelet, J. Am. Chem. Soc. 2006, 128, 3112. P.Y. Toullec, E. Genin, S. Antoniotti, J.-P. Genêt, V. Michelet, Synlett 2008, 707.
5. V. Michelet, P.Y. Toullec, J.-P. Genêt, Angew. Chem. Int. Ed. 2008, 47, 4268. E. Jiménez-Nuñez, A. M. Echevarren, Chem. Rev. 2008, 108, 3326. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351.
6. P. Y. Toullec, T. Blarre, V. Michelet, Org. Lett. 2009, 11, 2888. E. Genin, L. Leseurre, P. Y. Toullec, J. P. Genêt, V. Michelet, Synlett 2007, 1780. L. Leseurre, P. Y. Toullec, J. P. Genêt, V. Michelet, Org. Lett. 2007, 47, 4268. P. Y. Toullec, E. Genin, L. Leseurre, J. P. Genêt, V. Michelet, Angew. Chem. Int. Ed. 2006, 45, 7427. V. Michelet, L. Charruault, S. Gladiali, J.-P. Genêt, Pure & Appl. Chem. 2006, 78, 397.
7. C.-M. Chao, M. Vitale, P. Y. Toullec, J.-P. Genêt, V. Michelet, Chem. Eur. J. 2009, 15, 1319. P.Y. Toullec, C.-M. Chao, Q. Chen, S. Gladiali, J.-P. Genêt, V. Michelet, Adv. Synth. Catal. 2008, 350, 2401. C.-M. Chao, D. Beltrami, P. Y. Toullec, V. Michelet, Chem. Commun. 2009, 6988. L. Charruault, V. Michelet, R. Taras, S. Gladiali, J.-P. Genêt, Chem. Commun. 2004, 850.

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